WO2016006662A1 - Vernis de transport de charge, film mince de transport de charge et son procédé de fabrication, et élément électroluminescent organique et son procédé de fabrication - Google Patents

Vernis de transport de charge, film mince de transport de charge et son procédé de fabrication, et élément électroluminescent organique et son procédé de fabrication Download PDF

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WO2016006662A1
WO2016006662A1 PCT/JP2015/069787 JP2015069787W WO2016006662A1 WO 2016006662 A1 WO2016006662 A1 WO 2016006662A1 JP 2015069787 W JP2015069787 W JP 2015069787W WO 2016006662 A1 WO2016006662 A1 WO 2016006662A1
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group
charge transporting
bis
carbon atoms
thin film
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PCT/JP2015/069787
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English (en)
Japanese (ja)
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太一 中澤
彰治 森山
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日産化学工業株式会社
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Priority to US15/324,563 priority Critical patent/US10211412B2/en
Priority to KR1020177002188A priority patent/KR20170027790A/ko
Priority to EP15819759.0A priority patent/EP3168889B1/fr
Priority to CN201580037561.1A priority patent/CN106537628B/zh
Priority to JP2016532969A priority patent/JP6551693B2/ja
Publication of WO2016006662A1 publication Critical patent/WO2016006662A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
    • C09D5/24—Electrically-conducting paints
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H10K50/15—Hole transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/17—Carrier injection layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used

Definitions

  • the present invention relates to a charge transporting varnish, a charge transporting thin film and a manufacturing method thereof, and an organic electroluminescence element and a manufacturing method thereof.
  • organic EL element an organic electroluminescence (hereinafter referred to as organic EL) element is known as one of light emitting devices.
  • the organic EL element generally has a multilayer structure including an anode and a cathode, and a charge injection layer (a hole injection layer or an electron injection layer) and a light emitting layer disposed between the anode and the cathode, Light is emitted by recombining the injected electrons and holes in the light emitting layer.
  • a charge transporting thin film made of an organic compound is used for such a light emitting layer or charge injection layer.
  • the hole injection layer disposed between the anode and the light emitting layer is responsible for transferring charge to and from the anode and the light emitting layer, and has an important function for realizing low voltage driving and high luminance of the organic EL element. Fulfill. For this reason, for the purpose of improving the characteristics of the organic EL element, various studies have been made on charge transporting thin film forming materials for organic EL elements.
  • the method for forming the charge transporting thin film is roughly classified into a dry process typified by a vacuum deposition method and a wet process typified by a spin coating method. Comparing the two, the wet process has an advantage that it is easy to efficiently produce a thin film having a large area and high flatness.
  • Patent Documents 1 to 3 An example regarding a wet process material using an indolocarbazole derivative in which both two nitrogen atoms are not substituted has not yet been confirmed.
  • Non-Patent Document 1 describes only indolocarbazole compounds from the viewpoint of synthesizing indolocarbazole compounds, and the obtained indolocarbazole compounds are obtained by, for example, charge transporting thin films (hole injection layers and hole transports in organic EL devices). There is no description or suggestion of use as a layer.
  • the present invention has been made in view of such circumstances, and has a charge transporting property including an indolocarbazole derivative in which both of the two nitrogen atoms forming the indolocarbazole ring are not substituted as a charge transporting material.
  • An object is to provide a varnish, a charge transporting thin film obtained from the varnish, a method for producing the same, an organic EL device having the thin film, and a method for producing the same.
  • a charge transporting varnish which is an embodiment of the present invention that solves the above problems includes a charge transporting material composed of indolocarbazole represented by the following formula (1), a dopant material, and an organic solvent.
  • Z 1-substituted carbon atoms which may 6-20 aryl group, or heteroaryl of Z 1 is 2-20 carbon atoms substituted with R 1 and R 2 each independently represent a halogen atom, a nitro group, a cyano group, an amino group, a dimethylamino group, a hydroxy group, an alkoxy group having 1 to 20 carbon atoms, or substituted with Z 2.
  • n and m represent the number of R 1 and R 2 and are
  • the dopant substance preferably includes at least one of an aryl sulfonic acid compound and a heteropoly acid compound.
  • a charge transporting thin film which is another embodiment of the present invention for solving the above-mentioned problems is characterized by comprising any of the charge transporting varnishes described above.
  • the method for producing a charge transporting thin film according to still another aspect of the present invention for solving the above problems includes a step of applying the charge transporting varnish described above on a substrate, a step of evaporating an organic solvent, It is characterized by having.
  • An organic electroluminescence device which is still another embodiment of the present invention for solving the above-mentioned problems is characterized by comprising the above-described charge transporting thin film.
  • the charge transporting thin film is preferably at least one of a hole injection layer and a hole transport layer.
  • a method for producing an organic electroluminescence element which is still another aspect of the present invention for solving the above-described problems is characterized by using the above-described charge transporting thin film.
  • the charge transporting varnish of the present invention includes a charge transporting material composed of an indolocarbazole derivative in which both of the two nitrogen atoms forming the indolocarbazole ring are not substituted, and a dopant material. Therefore, a thin film having excellent charge transportability can be produced by using the varnish. According to the charge transporting varnish of the present invention, a thin film excellent in charge transporting property can be suitably produced even when various wet processes capable of forming a film over a large area, such as a spin coating method and a slit coating method, are used. Therefore, the charge transporting varnish of the present invention can sufficiently cope with the recent progress in the field of organic EL devices.
  • the charge transport property in this specification is synonymous with electroconductivity, and is also synonymous with hole transport property.
  • the charge transporting substance itself may have charge transporting ability, or may exhibit charge transporting ability when used together with a dopant substance (electron accepting substance).
  • the charge transporting varnish may be a substance having a charge transporting property, and the solid film obtained thereby may have a charge transporting property.
  • the charge transporting varnish of the present embodiment includes a charge transporting substance represented by the following formula (1), a dopant substance, and an organic solvent. That is, in the charge transporting varnish of this embodiment, the charge transporting substance as a host material mainly responsible for the charge transporting function is dissolved in the organic solvent together with the dopant substance to the extent that it can be used in a wet process. Is. Among these, the charge transporting substance is composed of an indolocarbazole derivative in which both of the two nitrogen atoms are not substituted.
  • An example of forming a charge transporting thin film such as a hole injection layer of an organic EL element by a wet process using a charge transporting material made of such an indolocarbazole derivative is a novel one.
  • Ar 1 and Ar 2 are, independently of one another, an aryl group of Z 1 is - carbon atoms 6 be 20 substituted by, or Z 1 - 2 carbon atoms which may be substituted with 20 Represents a heteroaryl group.
  • R 1 and R 2 are each independently a halogen atom, a nitro group, a cyano group, an amino group, a dimethylamino group, a hydroxy group, an alkoxy group having 1 to 20 carbon atoms, or the number of carbon atoms that may be substituted with Z 2 1-20 alkyl group, an alkenyl group or an alkynyl group Z 2 is 2-20 carbon atoms substituted with Z 2 is 2-20 carbon atoms substituted with.
  • Z 1 is a halogen atom, a nitro group, a cyano group, an amino group, a dimethylamino group, a hydroxy group, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms that may be substituted with Z 2
  • Z 1 2 represents an alkenyl group having 2 to 20 carbon atoms which may be substituted with 2
  • Z 2 represents a halogen atom, a nitro group, a cyano group, an amino group, a dimethylamino group, a hydroxy group, or an alkoxy group having 1 to 20 carbon atoms.
  • n and m represent the numbers of R 1 and R 2 and are integers of 0 to 4 independently of each other.
  • the aryl group having 6 to 20 carbon atoms includes phenyl group, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group. , 3-phenanthryl group, 4-phenanthryl group, 9-phenanthryl group, 4-biphenyl group, 4-terphenyl group and the like.
  • heteroaryl group having 2 to 20 carbon atoms examples include 2-thienyl, 3-thienyl, 2-furanyl, 3-furanyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-imidazolyl, 4-imidazolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl group, etc. Can be mentioned.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • examples of the alkoxy group having 1 to 20 carbon atoms include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, isobutoxy group, s-butoxy group, t-butoxy group, and n-pentyl group. N-hexyloxy group, n-heptyloxy group, n-octyloxy group, n-nonyloxy group, n-decyloxy group and the like.
  • alkyl group having 1 to 20 carbon atoms may be linear, branched or cyclic, and may be a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s Linear or branched having 1 to 20 carbon atoms such as -butyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group and n-decyl group Chain alkyl group: cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl group, cyclodecyl group, bicyclobutyl group, bicyclopentyl group, bicyclobutyl
  • alkenyl group having 2 to 20 carbon atoms examples include ethenyl group, n-1-propenyl group, n-2-propenyl group, 1-methylethenyl group, n-1-butenyl group, n-2-butenyl group, n -3-butenyl group, 2-methyl-1-propenyl group, 2-methyl-2-propenyl group, 1-ethylethenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, n-1 -Pentenyl group, n-1-decenyl group, n-1-eicocenyl group and the like.
  • alkynyl group having 2 to 20 carbon atoms examples include ethynyl group, n-1-propynyl group, n-2-propynyl group, n-1-butynyl group, n-2-butynyl group, and n-3-butynyl group.
  • a charge transporting thin film excellent in charge transporting property can be suitably manufactured even when various wet processes that can be dissolved in an organic solvent together with a dopant material and can be formed into a large area are used. It becomes a charge transporting varnish.
  • charge transporting substance used in the present embodiment one that can realize solubility in an organic solvent and low molecular weight of the charge transporting varnish can be mentioned. According to this, it is possible to provide a charge transporting varnish that is easy to spread after coating. For example, by a wet process typified by a spin coating method, a charge transporting thin film having a large area and high flatness can be efficiently applied to a transparent electrode such as ITO or IZO. Manufacturing.
  • At least one of Ar 1 and Ar 2 in the above formulas (1) and (2) is an aryl group, and further Ar 1. And Ar 2 are more preferably aryl groups.
  • Z 1 is a halogen atom from the viewpoint of improving the charge transportability of the obtained thin film. Of these, fluorine is more preferable.
  • examples of the charge transporting substance used in the present embodiment include those represented by the following formulas (a-1) to (a-21).
  • a charge transporting varnish produced by dissolving these charge transporting materials in an organic solvent together with the dopant material as described above, a charge transporting thin film having excellent charge transporting properties can be produced.
  • These charge transport materials have a low molecular weight and are excellent in solubility in organic solvents. Therefore, by using the charge transporting varnish, it becomes possible to efficiently produce a charge transporting thin film having high flatness over a large area by a wet process.
  • charge transporting substance in the present embodiment can be synthesized using the method described in Non-Patent Document 1, that is, the following scheme.
  • the charging ratio of the compounds represented by formulas (3) to (5) (formula (3): formulas (4) and (5)) can be adjusted as appropriate with a ratio of about 1: 2.
  • the compounds represented by formulas (3) to (5) can be obtained by conventional methods, but commercially available products may be used.
  • the charge transporting material used in the present embodiment described above has a molecular weight of preferably 2,000 or less, more preferably 1,000 or less, considering solubility in an organic solvent.
  • the charge transporting substance may be used alone or in combination of two or more.
  • charge transporting substances may be used in combination as long as the gist of the present invention is not changed.
  • charge transporting substances include oligoaniline derivatives described in JP-A No. 2002-151272, oligoaniline compounds described in WO 2004/105446 pamphlet, and those described in WO 2005/043962 pamphlet.
  • an aniline derivative having a molecular weight of about 200 to 4,000 is preferable.
  • the dopant substance used for the charge transport varnish of the present embodiment is not particularly limited as long as it is soluble in an organic solvent contained in the charge transporting varnish, and can be appropriately selected and used.
  • the aryl sulfonic acid compound is preferable as the dopant substance, and the molecular weight thereof is preferably 3,000 or less in consideration of solubility in an organic solvent. Preferably it is 2,000 or less, More preferably, it is 1,000 or less.
  • Examples of the aryl sulfonic acid compound that can be suitably used as the dopant substance include those represented by the following formula (6) and formula (7).
  • a 1 represents O or S, and O is preferable.
  • a 2 represents a naphthalene ring or an anthracene ring, and a naphthalene ring is preferable.
  • a 3 represents a divalent to tetravalent perfluorobiphenyl group, l represents the number of bonds between A 1 and A 3, is an integer satisfying 2 ⁇ l ⁇ 4, A 3 is a divalent par It is preferably a fluorobiphenyl group and 1 is 2.
  • j represents the number of sulfonic acid groups bonded to A 2 and is an integer satisfying 1 ⁇ j ⁇ 4, and 2 is optimal.
  • a 4 to A 8 are independently of each other a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, a halogenated alkyl group having 1 to 20 carbon atoms, or a halogenated group having 2 to 20 carbon atoms.
  • An alkenyl group is represented, but at least three of A 4 to A 8 are halogen atoms.
  • halogenated alkyl group having 1 to 20 carbon atoms include those in which at least one hydrogen atom of the alkyl group having 1 to 20 carbon atoms is substituted with a halogen atom.
  • Specific examples include trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2,2-pentafluoroethyl group, 3,3,3-trifluoropropyl group, 2,2 , 3,3,3-pentafluoropropyl group, 1,1,2,2,3,3,3-heptafluoropropyl group, 4,4,4-trifluorobutyl group, 3,3,4,4, 4-pentafluorobutyl group, 2,2,3,3,4,4,4-heptafluorobutyl group, 1,1,2,2,3,3,4,4,4-nonafluorobutyl group, etc. Can be mentioned.
  • halogenated alkenyl group having 2 to 20 carbon atoms examples include those in which at least one hydrogen atom of the alkenyl group having 2 to 20 carbon atoms is substituted with a halogen atom.
  • Specific examples include a perfluorovinyl group, a perfluoropropenyl group (allyl group), a perfluorobutenyl group, and the like.
  • Other examples of the halogen atom and the alkyl group having 1 to 20 carbon atoms are the same as those described above, but the halogen atom is preferably a fluorine atom.
  • a 4 to A 8 are a hydrogen atom, a halogen atom, a cyano group, an alkyl group having 1 to 10 carbon atoms, a halogenated alkyl group having 1 to 10 carbon atoms, or an alkenyl halide having 2 to 10 carbon atoms.
  • at least three of A 4 to A 8 are preferably fluorine atoms, a hydrogen atom, a fluorine atom, a cyano group, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms.
  • it is a fluorinated alkyl group or a fluorinated alkenyl group having 2 to 5 carbon atoms
  • at least three of A 4 to A 8 are fluorine atoms, and are a hydrogen atom, a fluorine atom, a cyano group
  • it is a perfluoroalkyl group having 1 to 5 carbon atoms or a perfluoroalkenyl group having 1 to 5 carbon atoms
  • a 4 , A 5 and A 8 are fluorine atoms.
  • the perfluoroalkyl group is a group in which all hydrogen atoms of the alkyl group are substituted with fluorine atoms
  • the perfluoroalkenyl group is a group in which all hydrogen atoms of the alkenyl group are substituted with fluorine atoms.
  • K represents the number of sulfonic acid groups bonded to the naphthalene ring, and is an integer satisfying 1 ⁇ k ⁇ 4, preferably 2 to 4, and 2 is optimal.
  • Specific examples of the aryl sulfonic acid compound suitable as the dopant substance are as follows, for example.
  • the dopant substance is not limited to the above formulas (b-1) to (b-6), and an arylsulfonic acid compound having another structure is used together with the arylsulfonic acid compound or instead of the arylsulfonic acid compound. It may be used. Furthermore, you may make it use dopant substances (other dopant substances) other than an aryl sulfonic acid compound with the said aryl sulfonic acid compound, or it replaces with the said aryl sulfonic acid compound.
  • An example of a material suitable as such other dopant substance is a heteropolyacid compound.
  • a heteropolyacid compound as a dopant substance, not only high hole acceptability from a transparent electrode typified by indium tin oxide (ITO) and indium zinc oxide (IZO) but also a metal anode typified by aluminum
  • ITO indium tin oxide
  • IZO indium zinc oxide
  • aluminum a charge transporting thin film (a hole injection layer, a hole transport layer, or the like) having a high hole acceptability and excellent in charge transportability can be obtained.
  • the heteropolyacid compound typically has a structure in which a heteroatom is located at the center of the molecule, which is represented by a chemical structure of Keggin type represented by formula (C1) or Dawson type represented by formula (C2), and vanadium. It is a polyacid obtained by condensing an isopolyacid that is an oxygen acid such as (V), molybdenum (Mo), or tungsten (W) and an oxygen acid of a different element.
  • the oxygen acid of such a different element mainly include silicon (Si), phosphorus (P), and arsenic (As) oxygen acids.
  • heteropolyacid compound examples include phosphomolybdic acid, silicomolybdic acid, phosphotungstic acid, silicotungstic acid, and phosphotungstomolybdic acid. These may be used alone or in combination of two or more. Also good.
  • the heteropolyacid compound that can be used in the present embodiment is available as a commercial product, and can also be synthesized by a known method.
  • the dopant substance when the dopant substance is composed of a single heteropoly acid compound alone, the one heteropoly acid compound is preferably phosphotungstic acid or phosphomolybdic acid, and phosphotungstic acid is preferred.
  • a dopant substance consists of two or more types of heteropoly acid compounds, one of the two or more types of heteropoly acid compounds is preferably phosphotungstic acid or phosphomolybdic acid, and more preferably phosphotungstic acid.
  • the heteropolyacid compound is obtained as a commercial product or suitable according to a known synthesis method even if the number of elements is large or small from the structure represented by the general formula in quantitative analysis such as elemental analysis. As long as it is synthesized, it can be used in this embodiment.
  • the dopant material that can be used in the present embodiment is not limited to the above example, and other dopant materials that accept electrons can be used without departing from the scope of the present invention.
  • the dopant substance contained in the charge transporting varnish of this embodiment can be about 1.0 to 70.0 by mass ratio with respect to the charge transporting substance 1, but preferably 2.0 to 60. About 0, more preferably about 2.5 to 55.0, still more preferably about 2.5 to 30.0, still more preferably about 2.5 to 20.0, and still more preferably 2.5 to 10. It is about zero.
  • the dopant substance contained in the charge transportable varnish of this embodiment is not limited to one type, and two or more types of dopant substances may be used in combination.
  • the organic solvent used when preparing the charge transporting varnish is a highly soluble solvent (good) that can dissolve the charge transporting material and the dopant material well to such an extent that the charge transporting varnish can be used in a wet process.
  • Solvent examples include N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, 1,3-dimethyl-2-imidazolidinone, diethylene glycol monomethyl ether, propylene glycol monomethyl.
  • An organic solvent such as ether can be used. These solvents can be used alone or in combination of two or more, and the amount used can be 5 to 100% by mass with respect to the total solvent used in the varnish.
  • the organic solvent which can be used in this embodiment is not limited to the said example, It replaces with the said high solubility solvent, or it replaces with the said high solubility solvent, and the low polarity solvent (polarity lower than a high solubility solvent ( A poor solvent) can also be used.
  • low-polarity solvents solvent molecules are low in polarity and poor in solubility in high-polarity compounds, but depending on the type of solvent, it can be applied to the substrate by improving viscosity, reducing surface tension, imparting volatility, etc. In some cases, physical properties suitable for spraying or coating of various coating apparatuses can be imparted, and the corrosiveness to the coating apparatus can be reduced.
  • the varnish has a viscosity of 10 to 200 mPa ⁇ s, particularly 35 to 150 mPa ⁇ s at 25 ° C., and a boiling point of 50 to 300 ° C., particularly 150 to 250 ° C. at normal pressure (atmospheric pressure).
  • a viscosity of 10 to 200 mPa ⁇ s particularly 35 to 150 mPa ⁇ s at 25 ° C.
  • a boiling point of 50 to 300 ° C., particularly 150 to 250 ° C. at normal pressure (atmospheric pressure).
  • the addition ratio of the high-viscosity organic solvent with respect to the whole solvent used in the present embodiment is preferably within a range where no solid is precipitated, and the addition ratio is preferably 5 to 80% by mass as long as no solid is precipitated.
  • other solvents are used in an amount of 1 to 90% by mass, preferably based on the total solvent used in the varnish. It is also possible to mix at a ratio of 1 to 50% by mass.
  • the viscosity of the varnish of this embodiment is appropriately set according to the thickness of the charge transporting thin film to be produced and the solid content concentration, but is usually 1 to 50 mPa ⁇ s at 25 ° C. Further, the solid content concentration of the charge transporting varnish in the present embodiment is appropriately set in consideration of the viscosity and surface tension of the varnish, the thickness of the charge transporting thin film to be produced, etc. .1 to 10.0% by mass, and considering the improvement of varnish applicability, it is preferably 0.5 to 5.0% by mass, more preferably 1.0 to 3.0% by mass. .
  • a charge transporting thin film can be formed on a base material by applying the charge transporting varnish described above onto the base material and baking it.
  • the method for applying the varnish is not particularly limited, and examples thereof include a dipping method, a spin coating method, a transfer printing method, a roll coating method, a brush coating, an ink jet method, and a spray method. It is preferable to adjust the viscosity and the surface tension.
  • the firing atmosphere is usually an air atmosphere.
  • the firing temperature is appropriately set within a range of about 100 to 260 ° C. in consideration of the intended use of the resulting charge transporting thin film, the degree of charge transporting property imparted to the obtained charge transporting thin film, and the like.
  • the obtained charge transporting thin film is used as a hole injection layer of an organic EL device, it is preferably about 140 to 250 ° C., more preferably about 145 to 240 ° C.
  • a temperature change of two or more steps may be applied for the purpose of developing a higher uniform film forming property or causing the reaction to proceed on the base material. What is necessary is just to perform using suitable apparatuses, such as oven.
  • the thickness of the charge transporting thin film is not particularly limited, but is preferably 5 to 200 nm when used as a hole injection layer in an organic EL device.
  • a method of changing the film thickness there are methods such as changing the solid content concentration in the varnish and changing the amount of the solution on the substrate during coating.
  • Examples of materials used and methods for producing a low molecular weight organic EL device (hereinafter referred to as an OLED device) using the charge transporting varnish of the present embodiment include the following. It is not limited.
  • the electrode substrate to be used is preferably cleaned in advance by liquid cleaning with a detergent, alcohol, pure water or the like.
  • the anode substrate is subjected to surface treatment such as UV ozone treatment or oxygen-plasma treatment immediately before use. It is preferable.
  • the anode material is mainly composed of an organic material, the surface treatment may not be performed.
  • FIG. 1 is a cross-sectional view showing a configuration example of an OLED element having a charge transporting thin film (for example, a hole injection layer) of this embodiment.
  • the OLED element 1 of this embodiment is an example, the ITO substrate 12 (anode) by which ITO11 was patterned on the surface of the glass substrate 10, the positive hole injection layer 13, the positive hole transport layer 14, the light emitting layer 15, and electron injection
  • the layer 16 and the aluminum thin film 17 (cathode) can be sequentially laminated.
  • other layers may be added as long as the gist of the present invention is not limited.
  • An example of a method for producing the OLED element 1 is as follows.
  • the charge transporting varnish of this embodiment is applied to the ITO substrate 12 to be the anode and baked, and the hole injection layer 13 is produced on the ITO substrate 12.
  • This is introduced into a vacuum deposition apparatus, and a hole transport layer 14, a light emitting layer 15, an electron transport layer / hole block layer (not shown) provided as necessary, an electron injection layer 16, and an aluminum thin film that serves as a cathode, for example. 17 is sequentially deposited to form the OLED element 1.
  • an electron blocking layer may be provided between the light emitting layer 15 and the hole transport layer 14.
  • anode material examples include transparent electrodes typified by indium tin oxide (ITO) and indium zinc oxide (IZO), metal anodes typified by aluminum, alloys thereof, and the like. What performed the chemical conversion process is preferable. Polythiophene derivatives and polyaniline derivatives having high charge transporting properties can also be used.
  • metal anode examples include scandium, titanium, vanadium, chromium, manganese, iron, cobalt, nickel, copper, zinc, gallium, yttrium, zirconium, niobium, molybdenum, ruthenium, rhodium, and palladium.
  • Cadmium indium, scandium, lanthanum, cerium, praseodymium, neodymium, promethium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, hafnium, thallium, tungsten, rhenium, osmium, iridium, platinum, gold , Titanium, lead, bismuth and alloys thereof.
  • Examples of the material for forming the hole transport layer 14 include (triphenylamine) dimer derivatives, [(triphenylamine) dimer] spirodimers, N, N′-bis (naphthalen-1-yl) -N, N′— Bis (phenyl) -benzidine ( ⁇ -NPD), N, N′-bis (naphthalen-2-yl) -N, N′-bis (phenyl) -benzidine, N, N′-bis (3-methylphenyl) -N, N'-bis (phenyl) -benzidine, N, N'-bis (3-methylphenyl) -N, N'-bis (phenyl) -9,9-spirobifluorene, N, N'-bis (Naphthalen-1-yl) -N, N′-bis (phenyl) -9,9-spirobifluorene, N, N′-bis (Naphthalen-1-yl) -N, N′-bis (pheny
  • Materials for forming the light emitting layer 15 include tris (8-quinolinolato) aluminum (III) (Alq 3 ), bis (8-quinolinolato) zinc (II) (Znq 2 ), bis (2-methyl-8-quinolinolato) (P-Phenylphenolate) Aluminum (III) (BAlq), 4,4′-bis (2,2-diphenylvinyl) biphenyl, 9,10-di (naphthalen-2-yl) anthracene, 2-t-butyl -9,10-di (naphthalen-2-yl) anthracene, 2,7-bis [9,9-di (4-methylphenyl) -fluoren-2-yl] -9,9-di (4-methylphenyl) ) Fluorene, 2-methyl-9,10-bis (naphthalen-2-yl) anthracene, 2- (9,9-spirobifluoren-2-yl) -9,9-spirobi
  • luminescent dopants examples include 3- (2-benzothiazolyl) -7- (diethylamino) coumarin, 2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H, 5H, 11H-10-.
  • Materials for forming the electron transport layer / hole block layer include 8-hydroxyquinolinolate-lithium, 2,2 ′, 2 ′′-(1,3,5-benztolyl) -tris (1-phenyl-1 -H-benzimidazole), 2- (4-biphenyl) 5- (4-tert-butylphenyl) -1,3,4-oxadiazole, 2,9-dimethyl-4,7-diphenyl-1,10 -Phenanthroline, 4,7-diphenyl-1,10-phenanthroline, bis (2-methyl-8-quinolinolate) -4- (phenylphenolato) aluminum, 1,3-bis [2- (2,2'-bipyridine) -6-yl) -1,3,4-oxadiazo-5-yl] benzene, 6,6'-bis [5- (biphenyl-4-yl) -1,3,4-oxadiazo-2-yl]- 2, 2 ' Bipyridine, 3-
  • cathode material examples include aluminum, magnesium-silver alloy, aluminum-lithium alloy, lithium, sodium, potassium, cesium and the like.
  • material for forming the electron blocking layer examples include tris (phenylpyrazole) iridium.
  • the production method of the polymer organic EL element (hereinafter, referred to as PLED element) using the charge transporting varnish of the present embodiment is not particularly limited, and examples thereof include the following methods. That is, in the production of the OLED element 1, instead of performing the vacuum evaporation operation of the hole transport layer 14, the light emitting layer 15, the electron transport layer (not shown), and the electron injection layer 16, the hole transport polymer layer, the light emission By sequentially forming the conductive polymer layer, a PLED element having a charge transporting thin film formed by the charge transporting varnish of this embodiment can be produced.
  • the charge transporting varnish of the present embodiment is applied on the anode substrate to produce a hole injection layer by the above method, and a hole transporting polymer layer and a light emitting polymer layer are sequentially formed thereon. Then, a cathode electrode is vapor-deposited to obtain a PLED element.
  • the hole transporting polymer layer and the light emitting polymer layer can be formed by adding a solvent to a hole transporting polymer material or a light emitting polymer material, or a material obtained by adding a dopant substance to the hole transporting polymer material. And a method in which the film is formed by uniformly dispersing, coating the film on a hole injection layer or a hole transporting polymer layer, and firing each of them.
  • Examples of the light-emitting polymer material include polyfluorene derivatives such as poly (9,9-dialkylfluorene) (PDAF), poly (2-methoxy-5- (2′-ethylhexoxy) -1,4-phenylenevinylene) (MEH). And polyphenylene vinylene derivatives such as -PPV), polythiophene derivatives such as poly (3-alkylthiophene) (PAT), and polyvinylcarbazole (PVCz).
  • polyfluorene derivatives such as poly (9,9-dialkylfluorene) (PDAF), poly (2-methoxy-5- (2′-ethylhexoxy) -1,4-phenylenevinylene) (MEH).
  • polyphenylene vinylene derivatives such as -PPV
  • polythiophene derivatives such as poly (3-alkylthiophene) (PAT)
  • PVCz polyvinylcarbazole
  • Examples of the solvent include toluene, xylene, chloroform and the like, and examples of the dissolution or uniform dispersion method include stirring, heating and stirring, and ultrasonic dispersion.
  • the application method is not particularly limited, and examples thereof include an inkjet method, a spray method, a dipping method, a spin coating method, a transfer printing method, a roll coating method, and a brush coating method.
  • the coating is preferably performed under an inert gas such as nitrogen or argon.
  • an inert gas such as nitrogen or argon.
  • As a method of baking the method of heating with an oven or a hotplate in inert gas or in a vacuum is mentioned.
  • Substrate cleaning Choshu Industrial Co., Ltd. substrate cleaning equipment (decompressed plasma method)
  • Application of varnish Spin coater MS-A100 manufactured by Mikasa Co., Ltd.
  • Film thickness measurement Fine shape measuring machine Surfcorder ET-4000 manufactured by Kosaka Laboratory Ltd.
  • Transmittance measurement Visible ultraviolet absorption spectrum measuring device UV-3100PC manufactured by Shimadzu Corporation
  • Production of organic EL elements Multi-function vapor deposition system C-E2L1G1-N manufactured by Choshu Industry Co., Ltd. Measurement of brightness etc. of organic EL element: IV World measurement system manufactured by Tech World
  • Example 1-1 A mixture of 0.073 g (0.178 mmol) of A1 and an aryl sulfonic acid compound represented by the following formula (b-1) (hereinafter abbreviated as B1) 0.080 g (0.089 mmol) can be used in a nitrogen atmosphere.
  • B1 aryl sulfonic acid compound represented by the following formula (b-1)
  • DMI 1,3-dimethyl-2-imidazolidinone
  • the obtained yellow transparent solution was filtered using a PTFE filter having a pore size of 0.2 ⁇ m to obtain a yellow transparent charge transporting varnish (solid content concentration 2.0 mass%).
  • B1 was synthesized based on the description in International Publication No. 2006/025342.
  • Example 1-2 A yellow transparent charge transporting varnish was obtained in the same manner as in Example 1-1 except that a mixture of 0.061 g (0.136 mmol) of A1 and 0.092 g (0.102 mmol) of B1 was used (solid content) Concentration 2.0% by weight).
  • Example 1-3 A yellow transparent charge transporting varnish was obtained in the same manner as in Example 1-1, except that a mixture of 0.048 g (0.117 mmol) of A1 and 0.105 g (0.117 mmol) of B1 was used (solid content) Concentration 2.0% by weight).
  • Example 1-4 To a mixture of 0.048 g (0.117 mmol) of A1 and 0.105 g (0.117 mmol) of B1, 2.5 g of DMI was added under a nitrogen atmosphere to dissolve the mixture. To this solution, 3.75 g of cyclohexanol and 1.25 g of propylene glycol were added and sufficiently stirred. Thereafter, 0.015 g of a 1: 2 (mass ratio) mixed solvent of trimethoxy (3,3,3-trifluoropropyl) silane and tri (methoxyphenyl) silane was added and further stirred sufficiently to obtain a yellow transparent solution. . The resulting yellow transparent solution was filtered using a PTFE filter having a pore size of 0.2 ⁇ m to obtain a yellow transparent charge transporting varnish (solid content concentration 2.0 mass%).
  • Example 1-5 A yellow transparent charge transporting varnish was prepared in the same manner as in Example 1-1 except that a mixture of 0.046 g (0.114 mmol) of A1 and 0.186 g of phosphotungstic acid (manufactured by Kanto Chemical Co., Inc.) was used. Obtained (solid content concentration 3.0 mass%).
  • Example 1-6 To a mixture of 0.043 g (0.097 mmol) of A2 and 0.173 g of phosphotungstic acid, 5 g of DMI was added under a nitrogen atmosphere to dissolve the mixture. To this solution, 1.0 g of cyclohexanol and 1.0 g of propylene glycol were added and stirred well to obtain a yellow transparent solution. The obtained yellow transparent solution was filtered using a PTFE filter having a pore size of 0.2 ⁇ m to obtain a yellow transparent charge transporting varnish (solid content concentration: 3.0% by mass).
  • the transmittance of the produced charge transporting thin films ([Example 2-1] to [Example 2-6]) was measured.
  • the transmittance was obtained by scanning a wavelength of 400 to 800 nm which is a visible light region.
  • the average transmittance at 400 to 800 nm is as shown in Table 1 below.
  • the OLED element 1 shown in FIG. 1 was produced by the following method. That is, an ITO substrate 12 in which ITO 11 was patterned with a film thickness of 150 nm on the surface of a glass substrate 10 of 25 mm ⁇ 25 mm ⁇ 0.7 t was used as the substrate. The ITO substrate 12 was used after removing impurities on the surface using an O 2 plasma cleaning device (150 W, 30 seconds).
  • the varnish of [Example 1-1] was applied to the ITO substrate 12 using a spin coater, dried at 50 ° C. for 5 minutes, and further baked at 230 ° C. for 15 minutes, so that the ITO substrate 12 had a thickness of 30 nm.
  • a uniform charge transporting thin film (hole injection layer 13) was produced.
  • ⁇ -NPD hole transport layer 14
  • Alq 3 light emitting layer 15
  • lithium fluoride LiF; electron injection layer 16
  • Aluminum thin films 17 were sequentially laminated to obtain an OLED element 1.
  • the film thickness is 30 nm, 40 nm, 0.5 nm and 100 nm, respectively, the degree of vacuum is 1.0 ⁇ 10 ⁇ 5 Pa, the deposition rate is 0.02 nm / second for LiF, and 0.2 nm / second for other materials. Vapor deposition was performed.
  • the OLED element 1 was sealed with a sealing substrate when evaluating the characteristics. Sealing was performed according to the following procedure.
  • the OLED element 1 was placed between the sealing substrates, and the sealing substrates were bonded together with an adhesive.
  • HD-0771010W-40 manufactured by Dynic Co., Ltd. was placed in the sealing substrate together with the OLED element as a water replenisher.
  • Mores Moisture Cut WB90US (P) manufactured by MORESCO Co., Ltd. was used.
  • the bonded sealing substrate was irradiated with UV light (wavelength: 365 nm, irradiation amount: 6000 mJ / cm 2 ), and then annealed at 80 ° C. for 1 hour to cure the adhesive.
  • the characteristics relating to current density and luminance of the fabricated OLED elements were measured.
  • the current density and luminance at the driving voltage of 5 V are as shown in Table 2.
  • the area of the light emitting surface size of each element is 2 mm ⁇ 2 mm.
  • OLED element 1 low molecular organic EL element (OLED element), 10 glass substrate, 11 ITO, 12 ITO substrate (anode), 13 hole injection layer (charge transporting thin film), 14 hole transport layer, 15 light emitting layer, 16 electrons Injection layer, 17 aluminum thin film (cathode)

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Abstract

L'invention comprend: une substance de transport de charge composé d'un indolocarbazole représenté par la formule (1); une substance dopante; et un solvant organique.
PCT/JP2015/069787 2014-07-09 2015-07-09 Vernis de transport de charge, film mince de transport de charge et son procédé de fabrication, et élément électroluminescent organique et son procédé de fabrication WO2016006662A1 (fr)

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US15/324,563 US10211412B2 (en) 2014-07-09 2015-07-09 Charge-transporting varnish, charge-transporting thin film and method for manufacturing same, and organic electroluminescent element and method for manufacturing same
KR1020177002188A KR20170027790A (ko) 2014-07-09 2015-07-09 전하 수송성 바니시, 전하 수송성 박막 및 그 제조 방법, 그리고 유기 일렉트로 루미네선스 소자 및 그 제조 방법
EP15819759.0A EP3168889B1 (fr) 2014-07-09 2015-07-09 Vernis de transport de charge, film mince de transport de charge et son procédé de fabrication, et élément électroluminescent organique et son procédé de fabrication
CN201580037561.1A CN106537628B (zh) 2014-07-09 2015-07-09 电荷传输性清漆、电荷传输性薄膜及其制造方法、以及有机电致发光元件及其制造方法
JP2016532969A JP6551693B2 (ja) 2014-07-09 2015-07-09 電荷輸送性ワニス、電荷輸送性薄膜及びその製造方法、並びに有機エレクトロルミネッセンス素子及びその製造方法

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